Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/17814
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Type: Journal article
Title: A cyclodextrin molecular reactor for the regioselective synthesis of 1,5-disubstituted-1,2,3-triazoles
Author: Barr, L.
Lincoln, S.
Easton, C.
Citation: Supramolecular Chemistry, 2005; 17(7):547-555
Publisher: Gordon Breach Sci Publ Ltd
Issue Date: 2005
ISSN: 1061-0278
1029-0478
Statement of
Responsibility: 
Lorna Barr, Stephen F. Lincoln And Christopher J. Easton
Abstract: 6A-Deoxy-6A-propynamido-β-cyclodextrin reacts with 4-tert-butylphenyl azide in aqueous solution, to form the 5-(aminocarbonyl)-substituted triazole in preference to the 4-(aminocarbonyl)- substituted analogue, in a ratio of 25:1. The cyclodextrin moiety templates the reaction through the formation of a host-guest complex of the dipole with the dipolarophile, controlling the regio-selectivity of cycloaddition. In a control reaction under similar conditions, with propiolamide instead of the cyclodextrin derivative, 5- and 4-(aminocarbonyl)-1-(4-tert-butylphenyl)-1,2,3-triazole were formed in a ratio of 1:4. As well as reversing the regioselectivity, the cyclodextrin substituent increases the rate of cycloaddition, by at least two orders of magnitude for the reaction to give the 5-substituted cycloadduct. Even the rate of formation of the 4-substituted cycloadduct is increased by a factor of two. Less marked effects are observed with phenyl azide and 4-tert-butylbenzyl azide as dipoles. © 2005 Taylor & Francis.
Keywords: Molecular reactors
Triazoles
Cyclodextrins
Regio selectivity
Cycloadditions
Templates
DOI: 10.1080/10610270500329131
Appears in Collections:Aurora harvest 2
Chemistry publications
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